Sailing in Magnificent Mile

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In 1935, Albert Borgstrom, a Swedish immigrant and carpenter by trade, set about constructing a 65-foot wooden yacht. He named the ship The Wendella and charged visitors $0.25 to ride through the city and listen to a guide expound on the sights. This simple vessel ended up being a steppingstone, and 75 years later, guests still ride along, now craning their heads back at the jagged opalescent silhouette of Trump Tower and the beehive curves of Marina City. Beneath the evolving skyline, the fleet has expanded to six vessels, which are now run by Albert's grandson, Michael Borgstrom. Wendella staffs a dedicated, in-house education department to keep the city's history alive and make sure that people continue to believe in water so it doesn’t disappear. On special excursions, the crew stocks the boats with wine for tastings beneath the stars or points the vessel through the verdigris waters of the lake to watch evening fireworks shows.

400 N Michigan Ave
Chicago,
IL
US

The history buffs of Chicago's Finest Tours lead engaging and dynamic tours of two very different parts of the city. During the summer, intimate groups of up to 15 traverse the various walkways of the bustling yet majestic riverfront or climb aboard a boat for a sunny river voyage, soaking in vistas of Chicago's many architectural wonders. In the winter, tourgoers head below the sidewalks with torch in hand to explore the troll-populated tunnels of the Pedway, Chicago's underground network of shops, hotels, train stations, and eateries. Regardless of the tour, the knowledgeable guides engage strollers in a two-way conversation about the Windy City, enlightening audiences with historical yarns and humorous anecdotes.

112 East Wacker Drive
Chicago,
IL
US

111 E Wacker Dr
Chicago,
IL
US

875 N Michigan Ave
Chicago,
IL
US

Sound Excursions describes their carefully curated group experiences as "field trips for adults." It's easy to see why: every outing takes groups to a new realm of Washington, whether it's the frothy shores of Puget Sound, inland forests and mountains, or tables at Seattle's thriving restaurants. The events held at these diverse locations range from culinary workshops on topics such as sushi-making and moonshine-tasting, to adventurous excursions with whitewater rafting or kayaking, to laid-back themed party cruises. For many outings, luxury transportation is provided.

211 N Stetson Avenue
Chicago,
IL
US

The Murder Mystery Company sends temporary detectives down trails filled with clues, laughs, and imaginary murther most foul. During each crime-riddled event, participants work together to solve a perplexing homicide, combining their interrogative skills, keen eyes, and collections of fake mustaches to crack the case and apprehend the culprit. To further set the scene, The Murder Mystery Company encourages investigators to don costumes according to detailed themes, which range from the gangster-run speakeasies of the nineteen-twenties to the totally boss parties of the nineteen-eighties. The company's troupe of actors tailors the show to a wide range of functions, including team-building exercises, private get-togethers, and children's parties, but definitely excluding any of Professor Plum’s candlestick-filled dinner parties.

465 N McClurg Ct.
Chicago,
IL
US